filters

Search results; Over 1,000 homes in Radda in Chianti

Photo 1 of 29
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 69 reviews
Photo 1 of 29
Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 11 reviews
Photo 1 of 24
Flat in Radda in Chianti
Cottage
Individual host
4–9 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 35 reviews
Photo 1 of 29
Guest favourite
Holiday home in Radda in Chianti
Pineta on La Spugna - oasis of peace & relaxation
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Photo 1 of 25
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
Business host
1–6 Oct
5.0 out of 5 average rating, 31 reviews
Photo 1 of 29
Guest favourite
Villa in Castelnuovo dei Sabbioni
Villa Valdarno Chianti - Private Pool
Business host
26 Jun – 1 Jul
4.92 out of 5 average rating, 36 reviews
Photo 1 of 29
Guest favourite
Flat in Pieve di Panzano
Tabor ~ Foresteria San Leolino to Panzano
Individual host
12–17 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
22–27 Oct
4.96 out of 5 average rating, 246 reviews
Photo 1 of 29
Superhost
Villa in Gaiole in Chianti
Le Granchiaie
Business host
17–24 Oct
Photo 1 of 29
Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
Photo 1 of 16
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Photo 1 of 29
Guest favourite
Flat in San Gusmè
La Dimora del Luca
Individual host
22–27 Oct
4.98 out of 5 average rating, 171 reviews
Photo 1 of 29
Superhost
Apartment in Gaiole in Chianti
Casa Livio, a garden with a view
Business host
10–15 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Guest favourite
Villa in Gaiole in Chianti
Corte del Chianti Dependance
Business host
29 Apr – 4 May
5.0 out of 5 average rating, 6 reviews
Photo 1 of 29
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Home in Tregole
Romantic villa in the Chianti Classico
Business host
12–17 Oct